Prior to the present invention few literature references were available which disclosed carbamoyl halides. For example, British Pat. No. 1,226,450 which was published Mar. 31, 1971 disclosed certain N-substituted N-acylcarbamic acid halides of the formula: ##STR1## wherein R' represents alkyl, aralkyl, alkenyl aralkenyl, cycloalkyl, heterocyclic or aryl radicals, R.sup.2 represents alkyl or alkynyl radicals and X represents halogen. The reference further indicates that R.sup.1 and R.sup.2 may be optionally substituted with certain other groups. However, compounds wherein R.sup.1 is an alpha-haloalkyl were not disclosed.
British patent specification No. 1,232,930, published May 26, 1971 discloses compounds of the formula: ##STR2## wherein R.sub.3 represents a hydrogen atom or alkyl, and R.sub.4 represents an optionally substituted alkanoyl group particularly, acetyl, chloroacetyl, dichloroacetyl and trichloroacetyl.
Accordingly, one or more objects will be achieved by the practice of the present invention. It is an object of this invention to provide novel carbamoyl halides. Another object of this invention is to provide novel N-(alpha-haloacyl)-N-hydrocarbylcarbamoyl halides. A further object of this invention is to provide carbamoyl halides such as N-chloroacetyl-N-methylcarbamoyl chloride, N-chloroacetyl-N-propylcarbamoyl chloride, N-alpha-chloropropionyl-N-methylcarbamoyl chloride, N-bromoacetyl-N-methylcarbamoyl chloride, N-chloroacetyl-N-methylcarbamoyl fluoride, and the like. A still further object of this invention is to provide processes for the preparation of the novel carbamoyl halides. Another object is to provide carbamoyl halides which are useful for the preparation of alpha-haloacyl carbamates of oximes, phenols and alcohols and alpha-haloacyl ureas from amines. These and other objects will readily become apparent to those skilled in the art in the light of the teachings herein set forth.